Non-malodorous hair perming method

ABSTRACT

A hair perming method including a first, reduction step using cysteamine or salt thereof, and a second, oxidizing step, is characterized in that a composition containing a monoaldehyde compound in a cosmetically acceptable carrier is applied to the hair before or after the oxidizing step, whereby the residual odor of reducing agent may be controlled effectively.

The present invention relates to a new process for the permanentdeformation of hair using cysteamine as the principal reducing agent,this process comprising a particular treatment to combat against aresidual disagreeable odor impregnating the hair.

A known technique for effecting the permanent deformation of hairconsists in carrying out, in a first stage, the opening of the disulfidebonds of keratin using a composition containing a reducing agent(reduction stage), then, after having preferably rinsed the hair,reconstituting in a second stage the said disulfide bonds by applying,on the hair under tension, an oxidizing composition (oxidation stage,also called fixation stage) so as to impart to the hair the desireddefinitive form. The application of the reducing composition can becarried out before or after rolling the hair on curlers.

This technique of the permanent deformation of hair permitsindifferently to effect either a waving of the hair or a straighteningor uncurling of the hair.

The compositions to effect the first stage of a permanent operation aregenerally provided in the form of lotions, creams, gels or powders to bediluted in a liquid support, and preferably contain a thiol as thereducing agent.

Among the thiols envisioned to effect the first stage of a permanentoperation, cysteamine or 2-amino ethanethiol is considered particularlyfavorable to obtain good waving of the hair but it has been noted thatthe hair thus treated however develops a very disagreeable odor after aweek to a month.

This unpleasant odor is more particularly perceptible when the treatedhair is in the wet state or in a moist environment. Thus, the appearanceof unpleasant odors is quite particularly noticeable in hot and humidclimates or is even noticeable if the subject has a tendency to secretelarge amounts of sebum.

From the fact of this disadvantage, cysteamine as well as its salts,even in weak amounts, is not generally employed as the reducing agent ina process for the permanent deformation of hair.

After various studies, it has now been noted, in a surprising andunexpected manner, that it is possible to prevent the appearance ofunpleasant odors, due to the use of cysteamine or one of its salts byproceeding, before or after the fixation stage, to apply a compositioncontaining a mono-aldehydic compound in a cosmetically acceptablevehicle.

The present invention thus relates to a process for the permanentdeformation of hair comprising a reduction stage using a reducingcomposition containing cysteamine or one of its salts and an oxidationstage, this process being characterized by the fact that before or afterthe oxidation stage, a composition containing a mono-aldehydic compoundin a cosmetically acceptable vehicle is applied to the hair so as tocombat the residual disagreeable odor impregnating the hair.

There is employed as the mono-aldehydic compound in accordance with theinvention, formaldehyde or an aromatic aldehyde selected from 2,4,6-trihydroxybenzaldehyde, α-methyl-β-(p.tert.butyl phenyl)propionaldehyde, 2-methyl-4-(2,6,6-trimethyl-2(1)cyclohexene-1-yl)butanal, 2-hexyl-3-phenyl-2-propenal,3,4-dimethoxybenzaldehyde, 2,3,4-trimethoxybenzaldehyde,2,5-dimethoxybenzaldehyde and 4-hydroxy-3-methoxybenzaldehyde.

Preferably, the mono-aldehydic compound is used at a molar concentrationbetween 0.15 and 1.8 moles and more preferably between 0.22 and 0.8mole.

The cosmetically acceptable vehicle is an aqueous solution or analcoholic or hydroalcoholic solution of a lower aliphatic alcohol suchas ethanol or isopropanol.

In accordance with a preferred embodiment, according to the invention,the hair is rinsed with water prior to the application of thecomposition containing the mono-aldehydic compound.

The composition containing the mono-aldehydic compound can, however,contain various cosmetic ingredients such as, for example, an anionic,nonionic, amphoteric, zwitterionic or cationic surfactant, analkalinizing or acidifying agent, a preservative, a stabilizer, atreating agent such as cations and polymers, a dye, a sunscreen agent, athickening agent or a nacreous lustering agent.

According to the process of the invention, the composition containingthe mono-aldehydic compound is applied on the hair before or after theapplication of the oxidizing composition for a period of time rangingfrom 1 to 60 minutes. After this treatment, the hair can optionally berinsed with water, except when the mono-aldehydic compound isformaldehyde in which case it is systematically rinsed.

In accordance with a particularly preferred embodiment of the processaccording to the invention, the composition containing themono-aldehydic compound is applied to the hair before the oxidationstage, the hair having previously been rinsed with water after thereduction stage.

When, in accordance with the invention, the composition containing themon-aldehydic compound is applied after the oxidation stage, theapplication can be immediate or delayed in time and optionally repeatedone or several times.

In accordance with the invention, the cysteamine or one of its salts, ispresent in the reducing composition in an amount ranging from 2 to 15percent by weight based on the total weight of the reducing composition.The reducing composition can optionally contain a secondary reducingagent such as, for example, thioglycolic acid, glycerol thioglycolate orcysteine.

Preferably, the pH of the reducing composition is between 6 and 10 andis obtained using an alkaline agent such as, for example, ammonia,monoethanolamine, diethanolamine, triethanolamine, an ammonium oralkaline carbonate or bicarbonate, an alkaline hydroxide or with anacidifying agent such as, for example, hydrochloric acid, acetic acid,lactic acid, oxalic acid, boric acid, citric acid or phosphoric acid oreven by means of a buffer such as, for example, mono and dipotassiumphosphate and ammonium bicarbonate.

In accordance with a preferred embodiment of the invention, the reducingcomposition can also contain a surfactant of the nonionic, anionic,cationic or amphoteric type.

The reducing composition can also contain treating agents, activesubstances such as panthotenic acid, anti-hair loss agents,antipellicular agents, thickening agents, suspension agents,sequesterants, opacifiers, dyes, sunscreen filters as well as perfumesand preservatives and optionally other reducing agents.

The oxidizing composition is of the type currently employed and containsas the oxidizing agent, H₂ O₂, an alkaline bromate, a persalt, apolythionate or a mixture of an alkaline bromate and a persalt. Theconcentration of H₂ O₂ can vary from 1 to 20 volumes and preferably from1 to 10 volumes; the concentration of alkaline bromate from 2 to 12percent and that of the persalt from 0.1 to 15 percent by weightrelative to the total weight of the oxidizing composition. The pH of theoxidizing composition is generally between 2 and 8, but preferablybetween 3 and 6.

The following non-limiting examples are given as an illustration of theprocess of the present invention for the permanent deformation of hair.

EXAMPLES Example 1

On moistened hair, previously rolled up on rollers having a diameter of14 mm, the following reducing composition is applied:

Composition (A)

    ______________________________________                                        Cysteamine hydrochloride                                                                          11.3 g                                                    Oleocetyldimethylhydroxyethyl                                                                     0.39 g                                                    ammonium chloride, in aqueous                                                                     (active material)                                         solution at 30% of active material                                            Ammonia, sufficient for pH = 8.5                                              water, sufficient amount for                                                                      100 g                                                     ______________________________________                                    

After letting composition (A) act on the hair for 15 minutes, the hairis rinsed with running water and the following composition (B) isapplied to the hair:

Composition (B)

    ______________________________________                                        Formaldehyde             0.2 g                                                Water, sufficient amount for                                                                           100 g                                                ______________________________________                                    

Composition (B) is permitted to act on the hair for 15 minutes at whichtime the hair is again rinsed with running water before applying thefollowing oxidizing composition (C):

Composition (C)

    ______________________________________                                        H.sub.2 O.sub.2 in aqueous solution at                                                                  4.8 g                                               200 volumes                                                                   Citric acid, sufficient for pH = 3                                            Water, sufficient amount for                                                                            100 g                                               ______________________________________                                    

After having let the oxidizing composition (C) act on the hair for 5minutes, the hair is rinsed with water. The rollers are then removed andthe hair is dried.

The formation of unpleasant odors over time, even after moistening thehair, is not observed.

As a comparison, the same process is carried out but omitting thetreatment using composition (B). After a certain period of time it isnoted that the hair gives off an unpleasant odor.

COMPARATIVE STUDIES

A. Treatment before the oxidation stage:

Ten hair samples, each weighing about 2.5 g are treated using a shampooand then rinsed. On each of the samples the following reducingcomposition is applied:

    ______________________________________                                        Cysteamine hydrochloride    9.6 g                                             Tegobetaine                 1 g                                               Ammonia, 20% in water, sufficient                                             for pH = 8.5                                                                  Demineralized water, sufficient amount for                                                                100 g                                             ______________________________________                                    

After having let this reducing composition act on the hair samples for15 minutes, all ten of the hair samples are rinsed with water.

One of the samples is reserved as a control and the remaining nine hairsamples are treated, respectively, by the following 1 to 9 treatingcompositions:

    ______________________________________                                        Composition 1                                                                 2,4,6-trihydroxybenzaldehyde                                                                             7.7 g                                              Ethyl alcohol              50 g                                               Demineralized water, sufficient for                                                                      100 g                                              Composition 2                                                                 α-methyl-β-(p.tert.butylphenyl)                                                               8 g                                                propionaldehyde, sold under the                                               trade name "LILIAL" by Givaudan                                               Ethyl alcohol, sufficient for                                                                            100 g                                              Composition 3                                                                 2-methyl-4-(2,6,6-trimethyl-2(1)-                                                                        9.1 g                                              cyclohexene-1-yl) butanal, sold                                               under the trade name "CETONAL",                                               by Givaudan                                                                   Ethyl alcohol, sufficient for                                                                            100 g                                              Composition 4                                                                 3,4-dimethoxybenzaldehyde  6.2 g                                              Ethyl alcohol, sufficient for                                                                            50 g                                               Demineralized water, sufficient for                                                                      100 g                                              Composition 5                                                                 2,3,4-trimethoxybenzaldehyde                                                                             9.8 g                                              Ethyl alcohol, sufficient for                                                                            100 g                                              Composition 6                                                                 2,5-dimethoxybenzaldehyde  8.3 g                                              Ethyl alcohol, sufficient for                                                                            100 g                                              Composition 7                                                                 2-hexyl-3-phenyl-2-propenal, sold                                                                        10.8 g                                             under the trade name "HEXYL                                                   CINNAMIC ALDEHYDE", by Givaudan                                               Ethyl alcohol, sufficient for                                                                            100 g                                              Composition 8                                                                 Formaldehyde, 30% in water 3 g                                                Demineralized water, sufficient for                                                                      100 g                                              Composition 9                                                                 4-hydroxy-3-methoxybenzaldehyde                                                                          7.6 g                                              Ammonia, 20% in water, sufficient                                             for pH = 8.5                                                                  Demineralized water, sufficient for                                                                      100 g                                              ______________________________________                                    

After having let these composition act on their respective hair samplesfor about 15 minutes the hair samples are thoroughly rinsed and there isapplied to the nine hair samples thus treated and on the control samplean oxidizing composition constituted of:

    ______________________________________                                        H.sub.2 O.sub.2, at 8 volumes                                                                        100 g                                                  Citric acid, sufficient from pH = 3                                           ______________________________________                                    

After a contact time of 5 minutes, the ten hair samples are rinsed withwater.

After drying, the hair samples are suspended in separate compartmentsfor 4 days.

After the second day, the hair samples are shampooed, washed with waterand dried.

On the fourth day, the hair samples are sprayed with water and submittedto a panel of 4 persons, so as to determine if they emit any residualodor. The intensity of the odor is ranked according to the followingscale:

    ______________________________________                                               0         no odor                                                             1         very weak odor                                                      2         weak odor                                                           3         perceptible odor                                                    4         pronounced odor                                                     5         strong odor                                                         6         very strong odor.                                            ______________________________________                                    

The results obtained are set forth in the following table:

    ______________________________________                                        ♦Sample                                                                     Treatment  Average rating of                                      No.         Composition                                                                              perceived odor                                         ______________________________________                                         1 (Control)                                                                              --         5.75                                                    2          1          1                                                       3          2          1                                                       4          3          1.5                                                     5          4          1                                                       6          5          1                                                       7          6          3                                                       8          7          1.25                                                    9          8          2.25                                                   10          9          2                                                      ______________________________________                                    

As can be seen, the treatment of the hair samples between the reductionstage and the oxidation stage, using a composition containing amono-aldehydic compound, very strongly reduces the presence of residualodors. Only composition (6), applied to hair sample (7) and containing2,5-dimethoxybenzaldehyde gives a result perceptibly inferior to theother compositions.

B. Treatment after the oxidation stage

In accordance with the same operating procedures described above in partA, nine hair samples are treated using the following reducingcomposition:

    ______________________________________                                        Cysteamine hydrochloride  10 g                                                Glycerol thioglycolate    3.1 g                                               Tegobetaine               1 g                                                 Ammonia, 20% in water,                                                        sufficient for pH = 7.5                                                       Demineralized water, sufficient for                                                                     100 g                                               ______________________________________                                    

After having let this reducing composition remain in contact with thehair samples for 15 minutes, the hair samples are rinsed with water andthe following oxidizing composition is applied to the rinsed hairsamples:

    ______________________________________                                        H.sub.2 O.sub.2 at 8 volumes                                                                        100 g                                                   Citric acid, sufficient for pH = 3                                            ______________________________________                                    

After having let the oxidizing composition react on the hair samples for5 minutes, 8 of these samples (1 being reserved as a control) aretreated, respectively, with the following treating compositions Nos. 10to 17.

    ______________________________________                                        Composition 10                                                                2,4,6-trihydroxybenzaldehyde                                                                             6 g                                                Ethyl alcohol              50 g                                               Demineralized water, sufficient for                                                                      100 g                                              Composition 11                                                                α-methyl-β-(p-tert.butylphenyl)                                                               5 g                                                propionaldehyde                                                               Ethyl alcohol, sufficient for                                                                            100 g                                              Composition 12                                                                2-methyl-4-(2,6,6-trimethyl-2(1)-                                                                        5.2 g                                              cyclohexene-1-yl) butanal                                                     Ethyl alcohol, sufficient for                                                                            100 g                                              Composition 13                                                                3,4-dimethoxybenzaldehyde  4.2 g                                              Ethyl alcohol, sufficient for                                                                            50 g                                               Demineralized water, sufficient for                                                                      100 g                                              Composition 14                                                                2,3,4-trimethoxybenzaldehyde                                                                             4.85 g                                             Ethyl alcohol, sufficient for                                                                            100 g                                              Composition 15                                                                2,2-dimethoxybenzaldehyde  5.8 g                                              Ethyl alcohol, sufficient for                                                                            100 g                                              Composition 16                                                                2-hexyl-3-phenyl-2-propenal                                                                              8.8 g                                              Ethyl alcohol, sufficient for                                                                            100 g                                              Composition 17                                                                4-hydroxy-3-methoxybenzaldehyde                                                                          6.8 g                                              Ammonia, 20% in water, sufficient for pH = 8.5                                Demineralized water, sufficient for                                                                      100 g                                              ______________________________________                                    

The hair samples, including the control sample, are submitted after 4days to a panel of 4 persons so as to determine if they give offresidual odors in accordance with the same scale as that given above inpart (A).

The results obtained are set forth in the following table:

    ______________________________________                                        Sample      Treatment  Average rating of                                      No.         composition                                                                              perceived odor                                         ______________________________________                                        1 (Control) --         5.75                                                   2           10         2.25                                                   3           11         2                                                      4           12         2                                                      5           13         1.75                                                   6           14         2                                                      7           15         3                                                      8           16         2.25                                                   9           17         1.75                                                   ______________________________________                                    

The results obtained show that with respect to the control sample, thereduction of the residual odor is quite significant. On comparing theresults of the treatment studies, before or after the oxidation stage,it can be noted in a surprising manner, that a more perceptiblereduction of residual odors is obtained when the composition containingthe mono-aldehydic compound is applied before the oxidizing composition.

We claim:
 1. A process for the permanent deformation of hair, comprisingthe steps of:(1) applying to said hair a reducing composition in anamount and for a time sufficient to reduce the disulfide bonds ofkeratin, said composition containing, as a reducing agent, cysteamine ora salt thereof, and (2) then applying to said hair, prior or subsequentto the application of an oxidizing composition to reform said disulfidebonds, a composition containing, in a cosmetically acceptable vehicle,an effective amount of a mono-aldehydic compound selected from the groupconsisting of formaldehyde, α-methyl-β-(p-tert-butyl-phenyl)propionaldehyde, 2-methyl-4-(2,6,6-trimethyl-2(1)cyclohexene-1-yl)butanal and 2-hexyl-3-phenyl-2 propenal, said composition containingsaid mono-aldehydic compound being applied to said hair in an amount andfor a time sufficient to prevent the unpleasant odors of the reducingagent.
 2. Process according to claim 1, wherein said mono-aldehydiccompound is present in a molar concentration between 0.15 and 1.8 mole.3. Process according to claim 1, wherein said cosmetically acceptablevehicle is an aqueous solution or an alcoholic or hydroalcoholicsolution of a lower aliphatic alcohol.
 4. Process according to claim 1,wherein said composition containing the mono-aldehydic compound furthercontains at least one cosmetic ingredient selected from the groupconsisting of an anionic, nonionic or amphoteric or zwitterionic orcationic surfactant, an alkalinizing or acidifying agent, a preservativeagent, a stabilizer, a treating agent, a dye, a solar filter, athickening agent and a nacreous lustering agent.
 5. Process according toclaim 1, wherein said hair is rinsed with water prior to the applicationof the composition containing the mono-aldehydic compound.
 6. Processaccording to claim 1, wherein said composition containing themono-aldehydic compound is applied on the hair during a time of 1 to 60minutes.
 7. Process according to claim 1, wherein said compositioncontaining the mono-aldehydic compound is applied on the hair before theoxidation stage, the hair having previously been rinsed with water afterthe reduction stage.
 8. Process according to claim 1 wherein an aqueouscomposition of formaldehyde is applied to the hair and then the hair isrinsed with water.